N-((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide → N-((S)-3-{2-Ethyl-4-[5-(2-isobutylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide
Reaction equation
[CH2:1]([C:3]1[CH:18]=[C:17]([C:19]2[N:23]=C(C3C=C(C)N=C(NCC)N=3)O[N:20]=2)[CH:16]=[C:15]([CH3:34])[C:4]=1[O:5][CH2:6][C@@H:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])[CH3:2].[CH2:35]([NH:39][C:40]1[N:45]=[C:44]([C:46]([OH:48])=O)[CH:43]=[C:42]([CH3:49])[N:41]=1)[CH:36]([CH3:38])[CH3:37]>>[CH2:1]([C:3]1[CH:18]=[C:17]([C:19]2[N:23]=[C:46]([C:44]3[CH:43]=[C:42]([CH3:49])[N:41]=[C:40]([NH:39][CH2:35][CH:36]([CH3:37])[CH3:38])[N:45]=3)[O:48][N:20]=2)[CH:16]=[C:15]([CH3:34])[C:4]=1[O:5][CH2:6][C@@H:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
N—((S)-3-{2-Ethyl-4-[5-(2-isobutylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide is prepared in analogy to N—((S)-3-{2-ethyl-4-[5-(2-ethylamino-6-methyl-pyrimidin-4-yl)-[1,2,4]oxadiazol-3-yl]-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide using 2-isobutylamino-6-methyl-pyrimidine-4-carboxylic acid; LC-MS: tR=0.96 min; [M+H]+=499.25. 1H NMR (D6-DMSO): δ 0.92 (d, J=6.5 Hz, 6H), 1.22 (t, J=7.5 Hz, 3H), 1.91 (m, 1H), 2.35 (s, 3H), 2.41 (s, 3H), 2.73 (q, J=7.5 Hz, 2H), 3.15-3.28 (m, 3H), 3.43 (m, 1H), 3.70-3.80 (m, 2H), 3.84 (d, J=4.8 Hz, 2H), 3.96 (m, 1H), 5.30 (d, J=5.0 Hz, 1H), 5.55 (m, 1H), 7.29 (s, 1H), 7.69 (m, 2H), 7.78 (s, 2H).
Sources & evidence
- ORD record
- ord-472693f4c5b24028aa4dceffaaf3ee94
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299086B2
Reaction notes
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